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$102+ Cheap flights from Chicago (CHI) to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Dec 24 — Dec 311
Tue 12/24
Tue 12/31
1 adult, Economy
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Cheap flight deals from Chicago to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 19, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$252
(Kiwi.com)

One-way from

$102
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$500
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
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From Chicago (CHI) to Winnipeg
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One-way flight from Chicago (CHI) to Winnipeg
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High demand for flights, 7% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in December 2024
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Find flight deals from Chicago to Winnipeg

Cheapest flights from Chicago to Winnipeg
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 19, 2024.

This Mytrip deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/267:00 amORD - YWG
2 stops16h 50mMultiple Airlines
Wed 1/87:30 amYWG - ORD
2 stops11h 49mMultiple Airlines
Deal found 12/18$641
This Air Canada deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2612:56 pmORD - YWG
Nonstop2h 32mAir Canada
Wed 1/87:30 amYWG - ORD
1 stop7h 21mAir Canada
Deal found 12/18$686
This Justfly.com deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/266:20 amORD - YWG
1 stop10h 34mWestJet
Wed 1/88:00 pmYWG - ORD
2 stops16h 55mWestJet
Deal found 12/18$721
This United Airlines deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2612:56 pmORD - YWG
Nonstop2h 32mUnited Airlines
Wed 1/82:15 pmYWG - ORD
Nonstop2h 36mUnited Airlines
Deal found 12/18$745
This Trip.com deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2611:25 amMDW - YWG
1 stop12h 25mMultiple Airlines
Wed 1/86:00 amYWG - MDW
2 stops11h 47mMultiple Airlines
Deal found 12/18$757
This FlightHub deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2611:25 amMDW - YWG
1 stop23h 20mPorter Airlines
Wed 1/87:00 pmYWG - MDW
1 stop17h 10mPorter Airlines
Deal found 12/18$804
This Delta deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/256:20 amORD - YWG
1 stop5h 32mDelta
Sat 1/46:55 amYWG - ORD
1 stop7h 43mDelta
Deal found 12/18$899
This Delta deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/254:50 pmMDW - YWG
1 stop6h 53mDelta
Sat 1/46:55 amYWG - MDW
1 stop4h 13mDelta
Deal found 12/18$952
This CheapOair deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2511:48 amMDW - YWG
2 stops11h 32mWestJet
Sat 1/45:44 pmYWG - MDW
1 stop17h 24mWestJet
Deal found 12/18$1,033

Find flights from Chicago to Winnipeg within your budget

Customize your flight search to find flights from Chicago to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 19, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 1/25

6:20 am-8:07 pm

2 stops13h 47m

Winnipeg

Mon 1/27

7:30 am-10:27 pm

1 stop14h 57m

$245

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 1/17

6:40 am-3:10 pm

1 stop8h 30m

Winnipeg

Tue 1/28

7:30 am-4:16 pm

1 stop8h 46m

$252

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 1/21

8:50 am-9:10 pm

1 stop12h 20m

Winnipeg

Fri 1/24

7:30 am-2:51 pm

1 stop7h 21m

$422

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 1/21

10:19 am-11:25 am

3 stops25h 06m

Winnipeg

Fri 1/24

8:00 pm-10:36 am

2 stops14h 36m

$476

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/10

1:40 pm-12:35 am

2 stops10h 55m

Winnipeg

Mon 1/13

8:00 pm-4:13 pm

2 stops20h 13m

$481

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 1/21

7:10 am-1:27 pm

1 stop6h 17m

Winnipeg

Fri 1/24

12:15 pm-11:28 am

2 stops23h 13m

$537

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 1/22

10:19 am-4:47 pm

1 stop6h 28m

Winnipeg

Fri 1/24

6:55 am-12:46 pm

1 stop5h 51m

$565

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 1/15

4:15 pm-11:42 pm

1 stop7h 27m

Winnipeg

Wed 1/22

12:45 pm-11:59 pm

2 stops11h 14m

$607

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 2/21

1:05 pm-6:04 pm

2 stops28h 59m

Winnipeg

Sun 2/23

11:35 am-12:10 pm

2 stops24h 35m

$665

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 1/27

1:03 am-11:25 am

2 stops34h 22m

Winnipeg

Fri 2/7

8:00 pm-11:21 pm

2 stops27h 21m

$2,108

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 17 results
1
2

Compare providers for flights from Chicago to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Winnipeg in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Winnipeg

Get recent, data-driven insights about flights from Chicago to Winnipeg including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago to Winnipeg?

Currently, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in February is currently the most expensive (average of $521). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to YWG?

Find hourly flight availability from Chicago to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 19, 2024.

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 18% on airfare.

What is the cheapest day to fly from Chicago to Winnipeg?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Winnipeg. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Winnipeg flight should consider departing on Thursday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated December 19, 2024.
See what other customers who have flown with Air Canada, WestJet and United Airlines from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,600 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,600 reviews
Delta
8.0
Very good
8,600 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Porter Airlines
7.9
Good
283 reviews
Delta
8.0
Very good
8,600 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Aeromexico
7.5
Good
1,924 reviews
Delta
8.0
Very good
8,600 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
9,048 reviews
Delta
8.0
Very good
8,600 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet
7.3
Good
2,819 reviews
Delta
8.0
Very good
8,600 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Chicago?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 1 inbound flight from Chicago per day from 3 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • What are the cheapest airlines flying from Chicago to Winnipeg round-trip?

    Flying on Air Canada is currently your cheapest option to Winnipeg, with prices starting at $399. Additional round-trip tickets that might be worth considering are offered by WestJet and United Airlines, with the lowest prices starting at $453 and $537, respectively. These flights start at 28% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Winnipeg one-way?

    One-way options have recently been found by users for as low as $193 on Air Canada. Other airlines that offer cheap prices include WestJet from $215 and Porter Airlines from $302 one-way.

  • What are the most reliable airlines from Chicago to Winnipeg?

    The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (90%), Air Canada (90%) and United Airlines (90%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $171. On average you can expect to pay $808. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $240.

  • Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Chicago to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Winnipeg.

  • Can I find deals for business class flights from Chicago to Winnipeg?

    Yes. Cheapflights offers flight deals from Chicago to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in February is currently the most expensive (average of $521). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Winnipeg flights
Midway to Winnipeg flights
St. Louis to Winnipeg flights

Top 3 airlines flying from Chicago to Winnipeg

Discover the top 3 airlines that operate flights from Chicago to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$219Average$570FlexibilityNo cancel feeOn-time67%
DeltaCheapest$510Average$618FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$535Average$710FlexibilityNo cancel feeOn-time69%
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